781592-33-4

Upstream product

• 175790-74-6 (S)-Azido-cyclohexyl-acetonitrile 
• 881813-31-6 (S)-N-(mesitylenesulfonyl)-α-(cyano)cyclohexylmethylamine 
• 943249-67-0 cyclohexanecarboxaldehyde N-(mesitylenesulfonyl)imine 
• 881812-42-6 N-(mesitylenesulfonyl)-α-(p-toluenesulfonyl)cyclohexylmethylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 148705-98-0 Toluene-4-sulfonic acid (R)-cyano-cyclohexyl-methyl ester 

Relevant academic research and scientific papers

Asymmetric Strecker reaction of aldimines using aqueous potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone

The phase-transfer-catalyzed, highly enantioselective cyanation of aldimines using aqueous KCN has been realized based on the molecular design of chiral quaternary ammonium iodide 2c bearing a stereochemically defined tetranaphthyl backbone. For example,

A convenient synthesis of (S)-2-azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines

(S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH4 into (S)-1,2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8·HCl in a saturated solution of HCl in alcohol gives (S)-2-amino carboxamide hydrochlorides (S)-10·HCl with enantiomeric excesses >99% after recrystallization.